Dimethylformamide → HCID 178509930, 화합물

HRID 505523노트

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HRID 505523 반응식
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[O:5][C:6]1[C:14]2[N:13]=[N:12][NH:11][C:10]=2[CH:9]=[CH:8][C:7]=1[Cl:15].[CH3:20][N:21](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N>[Cl:19][C:17]1[CH:18]=[C:2]([CH:3]=[C:4]([O:5][C:6]2[C:14]3[N:13]=[N:12][NH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[Cl:15])[CH:16]=1)[C:20]#[N:21]

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 1784778354-(3-bromo-5-chlorophenoxy)-5-chloro-1H-1,2,3-benzotriazole

생성물 1

HCID 178509930HCID 178509930, 화합물

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 8857Ethyl Acetate용매

실험 절차

4-(3-bromo-5-chlorophenoxy)-5-chloro-1H-1,2,3-benzotriazole (5.0 g, 14 mmol), tetrakis triphenylphosphine palladium (0) (4.83 g, 4.83 mmol) and zinc cyanide (1.96 g, 16.7 mmol) were suspended in dry DMF (50 mL) under N2 and placed in an oil bath at 90° C. After 2.5 hours, the reaction was allowed to cool to room temperature. The mixture was diluted with EtOAc (300 mL) and washed with water (4×100 mL), dried (MgSO4), filtered and concentrated with silica gel (20 g). This was purified by automated column chromatography on silica gel (120 g), eluting with 0-30% EtOAc/hexanes to deliver the title compound. LRMS (M+1)=304.8.

후처리

  1. customplaced in an oil bath at 90° C
  2. washwashed with water (4×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated with silica gel (20 g)
  6. customThis was purified by automated column chromatography on silica gel (120 g)
  7. washeluting with 0-30% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-ca405af8e237421d88ecbd04e65b6f9d
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781454B2

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